


Memoirs of a Lolita: First Times

by LittleDemonLoli



Series: Memoirs of a Lolita [1]
Category: Real Person Fiction
Genre: Age Difference, Consensual Underage Sex, F/M
Language: English
Status: Completed
Published: 2020-12-23
Updated: 2020-12-23
Packaged: 2021-03-11 05:34:50
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,388
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28260060
Author URL: https://archiveofourown.org/users/LittleDemonLoli/pseuds/LittleDemonLoli
Summary: Part of a series of fictionalized short stories based on my own experiences, from my POV. This story is about losing my virginity.
Series: Memoirs of a Lolita [1]
Series URL: https://archiveofourown.org/series/2070219
Comments: 2
Kudos: 6





	Memoirs of a Lolita: First Times

I had known that I was a kinky girl since I was super young. I had been looking at all kinds of weird fetish porn online since I was eight or nine, especially dirty stories. My favorites were the ones with pokemon fucking their trainers. I wasn't even masturbating correctly yet. Just torturing myself, rocking my hips in my chair in class or grinding into my pillows and plushies late at night. I was 12 by the time I had my first orgasm I can remember, after watching a girl in a video use her fingers to play with herself. It felt so amazing. All that tension and need building up before waves of release and pleasure. Once I knew how, I was playing with myself every day and night, as often as I could. If my parents weren't home I was reading filthy stories and rubbing my little pussy raw.

I had just started getting into fandom stuff and was hyped to go meet other nerds local to me. I knew most of them were going to be older than me and I had been given plenty of warnings from parents and teachers all my life about being alone around adults you don't know that well. I wasn't worried about that. I couldn't imagine at the time anyone could find me attractive and well, I was naive as hell. Besides... I WAS interested in sex. It's not my fault my flower started blooming early, so to speak. My parents are cool so I didn't need to convince them to let me go, but I had to find a ride. Thankfully the party had some folks willing to pick people up for gas money. That's how I first met David.

David was a nerd, and confident about it. Proud of it. Not the least bit ashamed of being awkward or different. Secretly I was just as much of an awkward nerd, just far less confident and far more ashamed. Back then I wanted so badly to look cool and hot and mature, not like some dumb little girl. The night of the party I had my brown hair in a ponytail and ball cap, big plastic sunglasses, halter top and cut off jeans. I was dressed to kill, at least in my 13 year old mind I was. He was dressed in jeans and a screen printed fan teeshirt. Meeting someone into the same geeky things I was into but with so little shame was instantly attractive and we immediately became friends. All through the party I was by his side tagging along, fishing for attention like a needy little sister. Most of the time I just hovered around him staying within his orbit. When the party got together to watch a movie, he let me cuddle with him. And when the party ended, he drove me home, dropped me off, and saw me to the door of my parents home. It wasn't a date, but it almost felt like one. And I really really liked it.

After the first party, David and I started to talk more online. We'd talk about fandom stuff, music, share art, and soon enough we were starting to get kind of affectionate towards one another. Inserting bits of RP into our chats, as if we were hugging, cuddling or more. For a little girl like me who THRIVED on attention, I couldn't get enough of it and I absolutely adored RPing online with him. So we did it more and more and with increasingly amorous narratives. When he asked me if I wanted to join him for next months party, I was thrilled. I spent the next couple weeks fantasizing about that next party and what fun I'd have with David.

I was so excited to go back again, to spend time with David. I couldn't get him out of my head. He was so funny and charming. And I loved meeting all the dorks and nerds at the last party, hanging out, cuddling and watching cartoons. From the moment he arrived and I stepped into his car, David and I were flirting and making dirty little jokes and references to each other. There was definitely more on our minds than just the party. Like last time I followed David like a lost puppy, basking in all of the attention and affection afforded to me by David and the rest of his friends. None of them knew me as the weird girl at school. Hell they probably WERE the weird kids when they went to school! It was like I had found my tribe. By the time we left it was getting really late, but I was still wired from how great I was feeling. So instead of taking me home, David offered to let me hang at his place and spend the night. I shot my mom a text to let her know not to expect me till tomorrow.

David's home was incredibly old, it was the kind of house kids might start rumors about being haunted and I loved it. It was rickety, it creaked as you walked around, you could smell the age in the air, but it was so warm and inviting too. David's room was especially inviting and comforting to me. He kept it dimly lit, and wall to wall his room was covered in his interests. Art on the walls both tame and erotic, comic books, sci-fi stuff, toys and games... It was a nerd lair, and it made me feel so at home. I liked those cartoons, those games and those toys, too. He showed me cartoons, we talked about art and music, and we continued to flirt and make filthy jokes. Filthy jokes that were slowly turning from jokes into little hints about what we were into. Things were getting pretty heated when I got up to use the bathroom. I had to pee but I also had all these thoughts in my head. Did he really like, LIKE ME like me?? He must, he wouldn't be flirting with me if he didn't find me attractive, right? I was also getting kind of horny...

I sat there getting myself all worked up thinking about the evening and thinking about David when the door opened with a creek and wearing a coy smile David said, "I thought you could use some help..."

I had been gone in the bathroom for so long he assumed I had been masturbating. And it's not like he was wrong about that either. I had totally been teasing and rubbing myself while wondering to myself if David was sending the signals I thought he was. I must have been quite a sight sitting on the toilet with my panties around my knees, my hand between my thighs in a futile attempt to hide what I had been doing. I was of course shocked, a little annoyed, a little scared, and very excited. It absolutely confirmed that he WAS into me, that's for sure. My first instinct of course was to get upset obviously, who wouldn't have that reaction to someone barging in on them in the bathroom? But there was this thought in my head that stuck out from my kneejerk reaction: Didn't you wanna try sex? This is your opportunity to see if you like it...

A timid "Okay..." was all I could manage to offer in response as he positioned himself in front of me, got on his knees and gently pushed mine apart while caressing his fingers up along my thighs.

He probably knew what the answer was going to be before I even showed up at his door that night. My bright blushing cheeks, shy nervous smile and the moistness on my peach fuzz pussy also gave me away. Each touch of his large rough hands against my sensitive skin felt electric. I leaned back against the toilet and sucked in a sudden gasp when he first touched my swollen sex and spread my eager little lips apart. As he explored my immature body it occurred to me that with the door behind him, if he wanted to David could keep me trapped in here. Something about that was so bizarrely thrilling to me, kinks show up in the most unexpected places sometimes. David hadn't even gotten me to bed yet and already he was already teaching me knew things about my body and sexuality.

I was already DtF from the last month of extended foreplay and the nights worth of teasing. He didn't need to slide his index finger into me knuckle deep and ask all quietly, "Has anyone else touched you like this before?"

"No no... never..." came my hushed, gasping reply.

Watching him molest my little sex, asking these questions, all the exciting thoughts racing through my mind, it was almost overwhelming how good it all felt together. I sat on his toilet trying to keep my voice low as I failed to fight back gasps, whimpers and moans. All while he helped himself to my body. Exploring my trembling thighs, my soft immature sex, he spread my legs further apart and took for himself a taste of my smooth drooling cunt. It was so hard to keep my voice down, squealing and giggling into my palm clasped over my mouth. His beard tickled me so much but his warm tongue and his soft lips felt soooo good.

Ever the tease David didn't let me enjoy his hard work too long before pulling away and asking, "Wanna head back to the bedroom now?" and lewdly licking his lips clean as if to let me know he was the pervy older man of my dreams.

He led me back to his room and to his bed before prompting me to undress myself, and going to get something from the top shelf of this big wooden dresser. I still get excited just thinking of the smell of the cheap passion fruit lube he used. No condom though. I knew I should say something but little 13 year old me was feeling horny and invincible. And besides, didn't I wanna know what it felt like to have a guy cum inside me? All I could think of was how good it must feel. So I didn't say a thing, and I knew he wasn't going to complain. I may have been barely a teenager but I knew the memes about guys hating condoms already.

So there we were.

Me, a naked 13 year old girl sitting on the bed of a naked 23 year old man, eagerly but nervously waiting for him to take my virginity.

He told me "Lay on your back", so I did.

He told me "Spread your thighs", so I did.

He began coating my puffy immature folds with lube, gently pumping his finger, then another, into my tight tender depths. My heart was absolutely racing and the anticipation only made my excitement more unbearable. He was so methodical and careful with how he handled me, just enjoying himself and taking his time, letting me get used to it as slowly and gently as he could.

As I moaned in delight on his fingers he'd ask me "Does this feel good?" or "Do you want to stop?" He knew from the noises I was making what my answers were going to be.

My parents had been teaching my about sex, consent, relationships and all that stuff since I was really little. My mom was an early bloomer too, and didn't want me to go out into the world unprepared. I hadn't had my period yet, but my mom already planned to put me on the pill as soon as I did just in case I "turned out like her", she would say before laughing it off. Turns out she was right.

"It feels amazing... Keep going, I love it..." I'd coo and purr as he got me so worked up and so slick, smearing sweet smelling lube across my puffy lips. I felt so safe in his hands, in his warm and cozy room. I laid naked on Davids bed looking up at him as he pulled me closer to his lap by my ankles and held me there. His glistening cock pressed to my needy underage mound and he began grinding into me. I knew he was going to push inside me soon. The room reeked of passion fruit lube and my little pussy. It was heaven.

"Are you sure you're ready? We can stop if you want to..." came the kind caring voice of David from above and between my ankles.

It was charming to me how careful he was trying to be. So cautious and considerate giving the naïve little girl that I was so many opportunities to back out and go home. But oh, was I ready alright. And the feeling of his big cock grinding back and forth against my clit, forcing my lips to spread again and again was so wonderful. Why would I want him to stop?

My heart was racing, I was trembling underneath him. "Don't stop... I want to feel it", I murmured in reply.

"It might hurt a little at first, just tell me if you want to stop okay? I'll go slow..." he rumbled like a lion, purring with pride as he spread my juicy little folds with his tip and pulled at my waist.

The soreness of him pushing into me and being spread around his member. The throbbing heat of him inside me. The electric pleasure running down my spine of him grinding into my clit as he fed me every inch. It was ecstasy. It was euphoria. He held my knees to his sides and slowly he began to slowly pump himself inside me, taking his time. He'd lean in and kiss my neck, or bite and growl affectionately into my ear to send jolts of pleasure through me, never stopping his slow steady thrusting. I didn't know just how sensitive my ears and neck were back then. I just melted underneath him, wriggling myself back into thrusts just like I had read in some of my filthy fanfics. It wasn't quite as painful as I expected. I guess masturbating with a glass soda bottle over the last month unintentionally helped prep me for my first time.

"Fuck. You are still so tight...", he growled into my ears between thrusts before pulling me into a deeper kiss than I'd ever had before.

I squeaked in shock and initially I was disgusted when he pushed his tongue into my mouth. It felt so weird and slimy at first, but as he slid his tongue along mine or bit at my lips while pumping himself into me, it started to send shivers down my spine. My arms slid up and wrapped around the back of his neck and I just held myself to his chest once our kiss broke. I could hear his heart beat and his ragged growls and gasps. The smell of his musk in his chest hair as he pressed me into his bed to thrust faster and faster. It was overwhelming, it was painful, it was exhilarating. The pleasure ringing all through me and the deep soreness of Davids steady thrusting creating an orchestra of bliss that was building and building within me.

David slid a hand down between us. "I want you to cum for me", he hissed, his thrusts short and deep while he gently teased his fingers over the hood of my tiny clit.

I was already putty in his hands and wasn't about to start saying no now. I was so wrapped up in what we were doing I couldn't bother with a response. I just held myself to him as tightly as I could and rocked my hips against his thrusts and rubbed my sore little cunt into his fingers. I wasn't just cumming for myself anymore, I wanted to cum FOR him. That was a new dynamic. Now he was telling me what to do. And I really liked it. Every thrust into me I would grind back into him, I wanted to cum for him so badly. I could feel the pressure building and building inside me while he pinned me to his bed. Until finally I stumbled past the point of no return while clinging to Davids chest.

"I'm d- doing it David... I'm cumming for you..." I stammered through desperate gasps, my voice muffled from underneath Davids chest.

I sang for him as my orgasm came crashing over me like a tidal wave. I squealed and moaned while bouncing underneath him, pinned to his bed. My body leaving the evidence of my pleasure as a wet spot on his sheets. There was little I could do besides lay still underneath him, and hold on tightly while I let this ocean of ecstasy wash me away. My body arched into his and my aching pussy eagerly flexed and clenched in delight to his rapidly quickening thrusts. David got his little girl to cum on him, and with his goal accomplished he needed to finish his own mission.

"Good." he growled, low and raspy. "That's... my girl." I could hear the concentration in his voice. I had seen plenty of guys cum in dirty videos but obviously never like this or so close, but I could tell that he was near his climax and I wanted him to cum inside me so badly.

He could spill himself inside me at any moment while I was in the throes of my own orgasm, and in that moment I couldn't desire anything more. Each thrust grew shorter as he held himself deep inside me. I loved how his balls would grind against my butt each time he'd push himself as deep as he could. His ragged gasping and low guttural growls and grunts against my ear sent shivers down my spine, and I still remember the quiet "oh, fuck" when he finally popped. As Rope after rope of his ripe seed began spilling into me, David bit down on my neck and shoulder HARD while grinding as deeply into me as could. The spreading molten warmth of his cum inside me radiated this gratifying bliss throughout every fiber of my little body. I sighed with such satisfaction underneath his shallow thrusts as he groaned, he was determined to keep every drop of his seed deep inside me.

For a while after David and I laid together just cuddling, kissing and gasping for breath. I felt so small and secure pinned underneath him, with his cock still inside me. We were exhausted, and neither of us wanted the night to end or for me to have to go home to my parents so soon the morning after. We held each other for a little while just talking about it, he'd ask me how I was feeling, if I enjoyed myself or how it felt. He was a horny guy but he could be so incredibly kind and considerate.

"Amazing..." I purred before saying, "I guess I'm not a little girl anymore now" or something equally lame like that. I don't know, I think it just sounded like the right thing to say after someone's first time. It sounds really cringy in retrospect.

After we got ourselves cleaned up a little bit, we cuddled and talked about nerdy shit and dirty jokes until we passed out. I hadn't slept so soundly before, cuddled up into the arms of a lover and still feeling the sore satisfaction of our gratuitous lovemaking. It was heavenly under those covers. I can remember being his little spoon. Him hugging me close in the dark warmth of his bedroom with my head against his chest, listening to his heart beat. I drifted off to sleep in his arms.

Someone once asked me as an adult, "What's one experience you'd relive for the first time again and again if you could?" and I couldn't give them the honest answer. If they only knew the truth... Most people might judge me or David for what we did together so long ago. They wouldn't understand what we had, what we felt. But I'd do it all again without a second thought.


End file.
